How to Win at Monopoly and Lose All Your Friends

INTRO: Why I hate Monopoly

If you just want to know how to win, scroll down to "EARLY GAME: Establishing the first monopoly". If, after reading the rest of the post, you have questions like "How could you do such a thing?" or "Why would you be so cruel?", this section contains the explanation. For various reasons, I think Monopoly is not that great of a game, but since everyone owns it, it still gets dragged out every once in a while.

Nobody knows how to play it, but they still end up hating each other.

Because Monopoly is one of the best-selling games of all time, most of us learned to play it as children. As such, most of us know the basics of going through a turn, such as rolling, moving, buying and improving properties, collecting rent and so on. However, few people know all the rules (more on this later) or how to form a cohesive strategy. This results in games were people more or less roll the dice and go through the motions until somebody wins. Because of the way the game is designed, this inevitably results in one person acquiring a majority of the assets on the board, and beginning the slow, painful, friendship-destroying process of grinding the other players out of the game, turn by turn. This is why Monopoly starts as a fun exciting romp, only to turn into a bitter cesspool of despair.

This is intentional!

Monopoly was, in fact, a rip-off of "The Landlord's Game", a game designed decades earlier by Elizabeth Magie, a proponent of Georgism (https://en.wikipedia.org/wiki/Georgism). The game was designed to teach children about the inherent unfairness of the capitalist land-grabbing system, and demonstrate how it enriches landlords while impoverishing tenants. Interestingly, it also included rules for a co-operative, anti-monopolist "Prosperity Game", in which victory was achieved when all players had at least double their original stake.

Make sure your friends never want to play Monopoly again.

I like board games, and I play them frequently. When the original Landlord's Game was developed, it was certainly fresh and innovative. However, 110+ years of advancement in the field of game design has produced games that are far superior, packing more strategy, nuance, and fun into a fraction of the play time. Monopoly is, by comparison, a long, boring, unpleasant slog. On the now-rare occasions that people insist I join a game of Monopoly, I play in a way that ensures not only that I'll win, but that they'll be more open to my suggestions for other games in the future.

PROTIP: Make sure the rulebook is handy

This strategy involves the use of rules that many people don't know about, and having the rulebook nearby will speed up the process of dealing with the numerous complaints you'll receive during the game.

EARLY GAME: Establishing the first Monopoly

Your goal in this portion of the game is to gain a monopoly and begin improving those properties. The earlier you can do this, the better, and a three-property group is far superior to a two-property group if you need to choose.

Step 1: Acquire properties

Begin more or less as you normally do, rolling and buying up whatever you land on. Once you start running out of money (say, $500 left), start working on the next step.
EDIT: Since a lot of people have brought this up (and it also seems to be something most people don't know), if someone lands on a property and doesn't buy it, either due to shortage of funds or not wanting to pay the list price, it is auctioned by the bank to the highest bidder. Landing on a property only gives the player first right of refusal to buy, not the right to prevent others from buying. This can sometimes be a good way to snag a cheap property, or pay extra to complete your set.

Step 2: Trade to acquire a monopoly on a group (Tip: "Poisoned colour sets")

It's extremely important that you do this as quickly as possible. If it means paying a stupidly high price, or even giving another player a monopoly at the same time, do it. You can force the other player out later.
Ideally, you want the cheaper properties (light blue, light purple, orange), which will allow you to build up houses faster. This will aid in creating a housing shortage, described later.
EDIT: /u/Minus-Celsius reminded me of a good tip, and gave it a fancy name, the "Poisoned colour set": It's better to go for the less expensive property groups, such as light blue, light purple, and orange, because they are easier to develop. With less experienced players, swapping an expensive property (e.g. green) for their cheap one (e.g. orange) to give you both a full set is an easy sell, but they end up with the "poisoned" set: something that's too expensive for them to develop with their current resources, while you sit on a set that can easily be developed with houses.
Bonus tip: In terms of probability, the orange properties will be hit the most, as they are 6, 8 and 9 spaces from jail, which is the most commonly occupied space on the board. If you have the opportunity to get the orange set, go for it.

Step 3: Improve your properties with three houses each

At this point, there should be a decent jump in your cash-flow from rent, and hopefully a bit of cash on hand. Spend the bulk of it on buying houses for your properties. Three houses on each is a good target, as there's a significant rent hike at the third house. It's worth mortgaging your other properties to do this faster, if possible.

MID-GAME: Establishing a second monopoly and creating a housing shortage

The goal in this stage is to gain a second monopoly, and buy enough houses to create a housing shortage, effectively locking down the game for the other players.

Rule Tip: Housing shortage

A little-known rule of Monopoly is that the game has exactly 32 houses and 12 hotels. Once you run out of houses, no more can be purchased until they re-enter the supply by being sold or upgraded to hotels. If there are more players who want to build houses than there are houses available, they are auctioned off to the highest bidder, one at a time. The core of this strategy is to buy up as many houses as possible before anyone realizes what you're doing, and DO NOT UPGRADE TO HOTELS to prevent people from improving their own properties.

Step 4: Second monopoly and more houses

Use rents on your improved properties to leverage other players into selling you the properties that you need for a second property group. If their rent exceeds their cash on hand, it's often easy to convince them to give you a property instead, particularly if it's for much more than they paid for it. Don't be too greedy here, it's more important to get the second monopoly. Any spare cash can be spent on improving your existing monopoly to four houses each.

Step 5: Housing shortage

With a second monopoly completed, your next task is to improve those properties to three houses each, then all of your properties to four houses each. Six properties with three houses will give you more than half of the houses in the game, and four houses each will give you 75% of the total supply. This will make it nearly impossible for your opponents to improve their own property in a meaningful way. Keep the rulebook nearby once the supply gets low, as you will undoubtedly be questioned on it. At this point, you will be asked repeatedly to build some friggin' hotels already so that other people can build houses. Don't.

END GAME: Frustration and despair

At this point, you more or less have the game sewn up. If losing a normal game of monopoly is frustrating, losing to this strategy is excruciating, as a losing opponent essentially has no path to victory, even with lucky rolls. Your goal is to play conservatively, lock up more resources, and let the other players lose by attrition. If you want to see these people again, I recommend not gloating, but simply state that you're playing to win, and that it wasn't your idea to play Monopoly in the first place.

Step 6: Build a cash buffer

With the high rents you're collecting, you should easily be able to float several hundred dollars at any given time. Your non-monopoly properties can be mortgaged for emergency cash. Since you should be bringing in more rent than you have going out, all you need to do is build up enough cash to protect your own monopolies from being broken if you have to pay rent to another player two or three times, or flipping the "Assessment for repairs" card. If you're fortunate enough to land in jail, stay there as long as you can and enjoy the rent-free turns.

Step 7: Wear down the resources of your opponents

Now is the time to stop accepting properties or other trade in lieu of rent. Force your opponents to sell off houses, mortgage properties, etc. This will protect you from taking any major rent hits during your own turns.

Step 8: Finish the game

Around this point, people will start quitting and giving the rest of their properties to the remaining opponents. With the bulk of that property unimproved or mortgaged, it won't do too much good. Now is the time to create a third monopoly, buy any remaining houses, and wait out the people who are still left. With the majority of the game's meaningful assets on your side of the table, it shouldn't take too long, and your opponents will have no way to fight back. Congratulations, you've won the game and everyone is furious.

POST-GAME: Go buy a better board game

As I mentioned in the intro, there are innumerable games superior to Monopoly that have been made in the last few decades. Most modern board games come with estimates of learning time, strategic complexity, and play time, which will help you to pick something appropriate for your group. Do some research on BoardGameGeek.com, and head down to your local gaming shop, where more often than not, you'll find knowledgeable staff and even demo sets for you to try before you buy. It shouldn't be too hard to convince your friends to try something new, especially if you offer to play another round of Monopoly.